Secrets of a Villainess
by DarkPheonix 666
Summary: Shego has been tormented with her sexuality for years and eventually comes out to Drakken after it begins to eat away at her After freeing herself from her cage; Shego decides to persue her redheaded ass kicking prey; But how will Kim feel knowing Shego wants her? Will she give into Shego's seduction? Or will she resist the desires of Shego? Kigo, KimxShego, Lesbian (Lemon later)
1. Chapter 1

Shego sat on her bed quietly pondering her thoughts. She had been thinking about her red headed nemesis for a while and a few other females. She would never tell anyone not even Drakken; but yes she was a lesbian.

She had known since she was but a young adolescent girl going through high school; a pretty young blonde named "Alicia" had been her classmate. During a lot of her first year Shego had masturbated over this girl and been drowning in angst over her.

Eventually during their senior year Shego had finally spoken to Alicia and even admitted her crush. The girl in return smiled and apologized saying she had a boyfriend but hoped Shego would find love.

At the time this had hurt Shego deeply and she had drowned her sorrows in beer and cried heavily. But it got better when she started college; she had developed better friendships and even a relationship.

The girls name was Jean; she was an art student and a huge nerd; however she was very cute and a closeted bisexual. The two dated for a long time during Shego's college years however later on Jean moved away causing them to break up which deeply hurt Shego.

Now in modern day she was working for a man-child Villain who went about world domination the wrong way and was an incompetent buffoon. But the pay was good and they had the same enemy so...she stayed. Her present relationships were few but still very passionate. Her hook-ups though had a large amount but happened when Drakken was never around.

But she longed for a proper relationship with someone; one filled with trust, loyalty, honesty and passion. She may have been evil but she still had feelings and desires like any other human being.

"DAMNIT!" Shego yelled crossly collapsing onto her pillow in frustration. As if being a villain wasn't stressful enough she had to deal with the complexities of her sexuality.

Suddenly there was a loud knocking on her door "Shego? Whats going on in there? Are you having another tantrum? You know I have to clean that up!" Drakken yelled sternly from the other side of the door.

Shego sighed heavily; her boss may have been a man-child but in subtle ways he showed he cared. He was like the dad she never had as her own had walked out her and her mother when she was a kid.

"Nothing Dr D; Just having a bad day" Shego grumbled crossly her head buried in her pillow.

Dr Drakken sighed heavily "Your always having a bad day Shego; your personality is like your menstruating 24/7. But you've always been fiery ever since I hired you as my henchwoman" he said solemnly.

Shego smiled to herself; as much as Drakken did get fed up with her moodiness, sullen attitude and temper he was good to her. He made sure to look after her now and again even though she was independent.

She opened her door via a switch under her desk; there may have only been one way into her room via outside but there was a way in via inside.

"Thank you" Drakken said gratefully as Shego allowed him to enter. His inner maternal instincts kicked in when he saw her troubled appearance. He said nothing as the door closed behind him.

He grabbed a nearby chair and sat beside her bed and folded his arms giving her a stern look. Something was up with his partner in crime and he needed to know what; he needed her to be her fully functioning sarcastic self like she always was.

"Now spill" Drakken said firmly. He wasn't going to leave until he knew what was going on and what was on her mind. He may have not been the brightest bulb in the world but he was a total idiot either.

"It's complicated" Shego muttered crossly. There was no way Drakken would understand any of this; if anything he would probably shit bricks.

"I got time" Drakken said causally with a cheeky smile. It was rather amusing to see Shego acting so much like a little kid. It was really quite adorable and it made him realize how much she hid her feelings.

Shego smiled impressed by this; as much as he annoyed her wasn't such a bad guy. She sat up still hugging the pillow for comfort and bowed her head.

"You know how everyone always asks why I don't have a boyfriend" Shego muttered shyly her face partially covered by her pillow.

Drakken nodded "Yes it the most popular topic among other villains; a few of which who fancy dating you" He said a hint of annoyance in his voice.

Shego was like a daughter to him; annoying, bitchy, short tempered and someone he knew not to piss off. But he cared about her a lot even if he didn't show it and hated how the other male villains treated her like a prize.

"And I'm always rejecting guys confessions and watching Orange is the new black" Shego stammered biting her lip.

"Mm hmm" Drakken said curiously raising an eyebrow suspiciously. She really had gotten into that show lately and yelled at anyone who disturbed her.

"And how I'm always getting so close to Possible and never seem to pay attention if we go somewhere crowded on business?" Shego whispered her body shaking.

"Yes" Drakken said in a slightly annoyed tone. He began to ponder all the things Shego was telling him all of these winding around the cogs in his brain.

 _Women; rejecting, gay shows and intimacy with the enemy_

Eventually Drakken's eyes widened and his jaw dropped; he was blown away by what Shego was saying and didn't know quite what to say.

"S...Shego you mean you're a...a...a.." Drakken stammered in shock. He had expected her to say she hated men but not this. He wasn't mad not at all...just mind blown.

"Lesbian" Shego said quietly fear hinting her tone. He was shocked now but he would probably be mad; I mean he always was about something.

Drakken shook his head and frowned at her crossly "Shego!..." he yelled crossly.

Shego began to shake and shrank where she was; she didn't know what he would do. I mean she could use her powers on him but she was too upset or troubled to. She closed her eyes and grabbed her pillow.

Suddenly she felt a hand on her head "Why didn't you just _tell_ me" Drakken said solemnly his tone more gentle.

Shego was taken aback by this; he wasn't mad? He wasn't going to yell at her? He wasn't going to throw her out?

She looked at him in awe her green eyes filled with shock "Y...You're not mad boss?" Shego asked in confusion.

Drakken gave her a baffled look "Why would I be? I mean you're still your green moody bitchy self despite your sexuality right?" he said crossly.

Shego's eyes welled up with tears and she hugged her boss happily; she hated his ass sometimes but she needed it today.

Drakken patted her back awkwardly just letting it happen; he wasn't a huggy person so he was just taking it quickly.

Eventually he pulled her off "Ok Ok don't get all mushy on me" he muttered crossly.

Shego sat there smiling gratefully her eyes glassy with tears; This had meant so much to her even if it didn't to him.

Drakken got up to leave "I'm off to order some more tools from a business partner; I'll just let you chill" he said awkwardly and left.

Shego sat there smiling to herself happily "Thanks Boss; that meant more than you know" she whispered.


	2. Shego's dating pool

Shego was sat on her bed reading comics; she was a huge fan of adventure time and Batman. They fed her love of action and kicking ass so she never got tired of them. Today she was having a slob day; she was wearing a black vest top and green khaki shorts with her hair in a ponytail.

Beside her was a huge bag of puffed crisps; chocolate milk and Reese's peanut butter cups. They were her favourites and she had an active lifestyle as a villain anyway so today she was splurging.

Suddenly Drakken entered her room with a tablet his face stern. He had some help for Shego in order to get her into dating. However it was risky considering her temper; but he was willing to try.

"What can I do for you boss?" Shego asked curiously taking a swig of chocolate milk. Since coming out they had been on better terms but still fought.

"I have something to show you" he said bluntly his tone hinting worry. He had no idea how she would react but he hoped it would be good.

"What is it?" she asked suspiciously. It had better not be some form of a joke or she would be mad as hell.

Drakken slowly approached the bed and sat showed her the tablet screen. It had apps such as Tinder, Grindr and Okcupid. All she had to do was set up an account and the dating pool begun.

"WOOOW; you really went all out" Shego said impressed. She never expected him to put so much effort in for her.

"Well you do seem to spend a lot of time alone; and who knows they may be fun. I'm sure they'll make interesting stories" Drakken teased mischievously.

"Shut up!" Shego hissed crossly her face flushing red. God why did he have to be so prude? What was a man's fascination with lesbians anyway?

Drakken ruffled her hair playfully "Lighten up Shego geez; I'm just kidding" he chuckled in amusement.

Shego frowned crossly and batted his hand away; he really was like her dad the way he messed with her like this. But she was doing her a huge favour which she greatly appreciated.

"I'll take a look at these now; so why don't you get your ass into the kitchen and give me space" She muttered a faint blush hinting her cheeks.

"Whatever you say" Drakken chuckled and went into the kitchen. It was times like this that reminded him she was a woman; because she didn't want to kill him as much.

Shego sighed heavily after he left; he wasn't exactly a jerk but he did know how to make her awkward and uncomfortable when she didn't want to be. Eventually she looked over the Ok cupid app since it was geared towards female in particular.

There were a lot of pretty girls on there that seemed to spark her interest but she decided to browse over them a while to get a bigger group of women in case she didn't like them. So far she had chosen the following women as they seemed to give off a not your average girl vibe.

Serina (23-bisexual) was a blonde haired girl who contrary to her princess appearance; dressed like a tomboy. She also a free lance artist and loved movies; but worked part time as a waitress.

Shego liked how she was reverse gender roles despite looking like a girly girl. She also must have been good with handling stress to have such an annoying job too. She added her to her favourite list and kept looking.

The second was Alice (21) a bluish green haired girl with a punk styled attire. She liked cartoons, anime and role-playing. She was a self defence teacher and a self help therapist part time. This one too was added to Shego's list due to the possibility of kinky sex being involved.

She was about to leave and go back to her comics when she spotted something that made her smile ear to ear.

Kim (16) Bisexual; Her very own enemy Kimmie was on a gay dating website and openly bisexual. She wondered deep down if she was hiding this from Ron or if he was even aware of their relationship.

This supposed waste of time had become so much more interesting. She could find herself two potential lovers while messing with Possible and making her taste the forbidden fruit. It would be so much fun messing with her this way.

"This just became so worth it" Shego chuckled and added Kim to her list. At first she thought this would be a pain in the ass; turned out it was more fun than she interpreted it.


	3. C3: Bumps in the road are nothing

Shego walked quietly into the bedroom; she had just gotten back from her date with Serina. She was really regretting the fact that she said YES and added her to favourites; what the fuck was she thinking?

She collapsed onto her bed sighing; she was wearing a black and green dress with heels. She kicked them off happily her face still buried in her bed.

"So how'd it go?" Drakken called casually as he walked in holding a cup of coffee. He had already figured out her mood by her angry stomps; the date had obviously been bad.

"Horrible" Shego muttered into her pillow.

"You seemed pretty keen on blondie before" Drakken said in a confused manner and placed the coffee on her bedside table.

Shego sat up slowly annoyance obvious in her face "She was cute sure; but turns out she only loves action movies with female stars and is all about female empowerment. When I mentioned I worked for you she went ape shit on our date" she explained crossly.

Drakken went quiet but connected the dots; despite being cute this girl was not what she seemed "Lemme guess feminazi?" he said sitting beside her on the bed.

"Yep" Shego sighed crossly. She had high hopes on this girl; but ultimately she was not what she wanted. The fact she called her weak and brainwashed for working as a henchwoman to an evil genius pissed her off. In the end Shego had blasted her with her plasma bolts and left her with the check.

Drakken patted her back sympathetically; he did feel bad for Shego he really did. But you had to go through some duds before you found the right one. "So you got two left right? What are these chicks like?" he asked curiously.

"Ones a blue haired bisexual part time self defence teacher with a love for anime, cartoons and role-playing..." Shego began casually taking her coffee and taking a long swig.

"She sounds fun" Drakken said hopefully. If she could fight and was interesting he wouldn't mind keeping her as a second henchwoman. Thus Shego would be happy and he would have an extra set of hands to kick Kim possible's ass.

"The other is a redhead who is a closeted bi girl; most likely her first same sex relationship. Looking for a relationship and lives in Middleton and is a high school student" Shego explained in an amused tone.

She was never going to tell Drakken she was going on a date with Kimmie; it was her precious secret and she could blackmail her for all it was worth. For the longest time she had been interested in her; but now she knew Kim _liked_ girls.

Drakken smirked "That's the same area which Kim Possible lives" he said thoughtfully.

Shego jumped out of her skin; had he figured it out? If so he was smarter than he let on "Yeah so?" she said curiously trying not to give herself away.

"While on your date you could spy on miss possible; maybe learn a few juicy secrets" Drakken said slyly.

Shego internally sighed a breath of relief; no he was still dense as ever "Sure boss can do" she lied.

Drakken was glad he got Shego into this dating pool; it was turning out quite beneficial for the both of them. His henchwoman was getting dates and he was getting peace and quiet to work on his projects.

He then smirked casually a hint of playfulness to it; Shego didn't like the look he was giving her and slightly cowered away. "What's that look for?" she asked worriedly.

"You know what they say about redheads" He teased biting his lip and stifling a laugh. She guessed he was going to make some lame joke.

"What?" she said suspiciously still a little creeped out. Jesus ever since she came out and started dating he had been acting weird.

"They're crazy in bed" Drakken said smugly wiggling his eyebrows. Yes he had just made a dirty joke; he was possible of such things at his age.

Shego blinked then imagined a scenario of such things with Kimmie in her bedroom. A large smirk appeared on her face and her eyes became wicked. Oh the things she would do to that girl.

"I don't doubt it Dr D; I can't wait to test the theory" she said mischievously her smirk getting bigger.

Drakken smiled; he had accomplished his mission by cheering up Shego. She could now enjoy her coffee while having her own fantasies about future dates. Now she could forget her crap date earlier.

He quietly slipped out leaving Shego with her thoughts; now that she was distracted he could have peace working. That and she could make plans for both of her future dates should they go well.

 _ **A short while later**_

Shego stripped out of her date clothes quietly and tossed them in her wardrobe; she then pulled on a black vest and green cargo shorts. Afterwards she tied her hair into a messy bun and sat atop her bed.

She opened her laptop and gazed at her two future babes; Alice the kinky cutie and Kimmie her redheaded rival. God she hoped that there was a possibility of a threesome. She wiped the drool from her mouth as a very vivid image came to her head. She would save it for later when she was bored.

She typed a message to both girls but made sure that they were different so they would not catch on. While she was interested in both girls she was an open minded individual but a serial monogamist.

To Alice- _"Hey cutie; I notice you love role playing and cosplay. Wanna have some fun with me?"_

Shego smiled deviously; that would get her attention no problem. If she didn't take the bait the girl was obviously an idiot.

To Kim- _"Hey Kimmie; didn't know you were into the sweeter side of the pool. Guess you really must love the bad girls" ;D_

Shego bit her lip stifling a laugh; while having an intense crush on Kim she loved teasing her nonstop. It was one of her many methods of flirting; 9 times out of 10 it usually worked.

She waited for a while waiting for them to reply. She didn't know how long it would take so she started taking notes for date ideas. Eventually she got a reply from Alice.

Alice to Shego- _"Do I ever; god you're so beautiful. I'd love to play maid and master with you any day"_

Shego smirked...yes this Alice girl was definitely a keeper. Thank god the date crashed and burned with that crazy blonde.

Kim to Shego- _"SHEGO?! What are you doing on here? Never mind! Please don't tell anyone!"_

Shego stifled a laugh; Kim was just as adorable when she was messaging. She was definitely panicking but she wasn't going to back down.

Shego to Alice- _"Sounds like fun baby doll; but Sensei wants an obedient pet. Are you sure you can handle being my toy?"_

She guessed that this Alice girl wanted to play top; but she tended to go top first. Then she didn't mind bottoming once she had gotten her fun watching her partner.

Shego to Kim- _"You know Kimmie; I've always thought you were a cutie; but I guess I'm not good enough to date little miss prim and proper"_

She already knew that would piss off Kim; flirting with her while making her feel bad about backing out. After all they could be a match but she wasn't willing to find out.

As soon as she sent them 2 replies came; she was having fun with this. She was flirting and teasing both girls. Something told her the dates would be better than the last one.

Alice to Shego _\- "The question is can you handle me being your pet? I can be quite a troublesome pet ;D"_

Shego smirked; yes this girl was a keeper. She was cute, cheeky, flirty and kinky. This made her glad things didn't work out with Blondie. She would have missed out on this gem.

Kim to Shego- _"I never said that! Look I'm sorry I just...I'm still in the closet and I really want to just try dating someone my gender. My family and Ron would never understand; Please Shego?"_

Shego felt bad after that message; she recalled coming out to her parents at Kim's age. They had thrown abuse at her and cried. Shortly after she moved out and got a place of her own; her parents had been assholes but she hoped Kimmie's weren't.

Coming out was never easy; there was pressure, fear, anxiety and sadness. Also the unpredictability of how the parents would react. She felt bad for Kim but at the same time she didn't want to let her go.

Shego to Alice- _"Baby; I can handle anything. How about me; you Friday night?"_

Shego to Kim- _"Kimmie I aint gonna tell anyone; However I would like to see you in something cute this weekend"_

She bit her lip anxiously; Alice was already good to go but Kim was being a bit more awkward. She really wanted this to go smoothly and as she wanted to fuck them both until they were sore.

She felt herself drooling at the thought of kinky sex with Alice and then watching Kim fall apart under her as she ate her out hard. Ugh she was spoilt for choice.

Alice to Shego-" _It's a date :D"_

Kim to Shego- _"...I guess it's a date then"_

Shego punched the air and made a eager "YEEESSS" sound. She had hit 2 birds with one stone and was going to finally go on a date with Kim. God things were finally going her way.

Eventually Drakken strolled by hearing her change in mood; quietly he poked his head in the door "I see things are going well" he said bluntly his tone positive.

Shego grinned at him "Got two dates this week Dr D; One with Alice on Friday and one with red this weekend" she said eagerly.

Drakken smiled "Somebody's getting laid" he teased in an amused tone. He had no doubt Shego would bring them back here so he would go stay with Monkey fist for the weekend.

"You betcha" Shego teased holding back a happy scream of joy.

"I'll make a call to Monty; I've been meaning to have drinks with him. Just don't make too much of a mess" Drakken said casually.

Shego leapt off the bed and hugged Drakken; he had accepted her sexuality. Found her dating sites and was now leaving her alone at the lair to bring home her dates. God he was the best boss ever...fuck what Serina said.

"You're the best Drakken" She said happily.

Drakken patted her back gently; despite being a hot headed violent villainess she was still human. She had her ok days but most were plain scary as hell.


End file.
